CN107868109A - Electroluminescent organic material and device - Google Patents
Electroluminescent organic material and device Download PDFInfo
- Publication number
- CN107868109A CN107868109A CN201710864619.0A CN201710864619A CN107868109A CN 107868109 A CN107868109 A CN 107868109A CN 201710864619 A CN201710864619 A CN 201710864619A CN 107868109 A CN107868109 A CN 107868109A
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- compound
- alkyl
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- 239000011368 organic material Substances 0.000 title abstract description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 91
- 125000003118 aryl group Chemical group 0.000 claims abstract description 59
- 239000000203 mixture Substances 0.000 claims abstract description 56
- 125000001424 substituent group Chemical group 0.000 claims abstract description 37
- 125000000217 alkyl group Chemical group 0.000 claims description 51
- 125000001072 heteroaryl group Chemical group 0.000 claims description 38
- 229910052799 carbon Inorganic materials 0.000 claims description 29
- -1 silylation Chemical group 0.000 claims description 27
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 26
- 239000012044 organic layer Substances 0.000 claims description 25
- 125000003342 alkenyl group Chemical group 0.000 claims description 23
- 125000000304 alkynyl group Chemical group 0.000 claims description 23
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 22
- 239000002184 metal Substances 0.000 claims description 22
- 229910052751 metal Inorganic materials 0.000 claims description 22
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 20
- 229910052736 halogen Inorganic materials 0.000 claims description 20
- 150000002367 halogens Chemical class 0.000 claims description 20
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 19
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 18
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 18
- 229910052805 deuterium Inorganic materials 0.000 claims description 18
- 150000002825 nitriles Chemical class 0.000 claims description 18
- 125000002252 acyl group Chemical group 0.000 claims description 17
- 125000004104 aryloxy group Chemical group 0.000 claims description 17
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 17
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 17
- 150000002148 esters Chemical class 0.000 claims description 17
- 150000002527 isonitriles Chemical class 0.000 claims description 17
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 17
- 238000006884 silylation reaction Methods 0.000 claims description 17
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 17
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 17
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 claims description 16
- 125000002769 thiazolinyl group Chemical group 0.000 claims description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 229910052710 silicon Inorganic materials 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 239000010703 silicon Substances 0.000 claims description 13
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 12
- 125000005580 triphenylene group Chemical group 0.000 claims description 12
- 239000003446 ligand Substances 0.000 claims description 10
- 125000005647 linker group Chemical group 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical class C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 9
- 238000007363 ring formation reaction Methods 0.000 claims description 9
- 150000004826 dibenzofurans Chemical class 0.000 claims description 8
- 238000005286 illumination Methods 0.000 claims description 7
- 125000000962 organic group Chemical group 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 150000001924 cycloalkanes Chemical class 0.000 claims description 6
- 229910052741 iridium Inorganic materials 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- GXGTZUUUEQORAH-UHFFFAOYSA-N C1=CC=CC=2SC3=C(C21)C=CC=C3.N3C=CC=CC=C3 Chemical class C1=CC=CC=2SC3=C(C21)C=CC=C3.N3C=CC=CC=C3 GXGTZUUUEQORAH-UHFFFAOYSA-N 0.000 claims description 5
- 229910052697 platinum Inorganic materials 0.000 claims description 5
- KDOKHBNNNHBVNJ-UHFFFAOYSA-N C1=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12.N1C=CC=CC=C1 Chemical group C1=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12.N1C=CC=CC=C1 KDOKHBNNNHBVNJ-UHFFFAOYSA-N 0.000 claims description 4
- MSJMEQRRQOBTRB-UHFFFAOYSA-N C1=CC=CC=2C3=CC=CC=C3NC12.N1C=CC=CC=C1 Chemical compound C1=CC=CC=2C3=CC=CC=C3NC12.N1C=CC=CC=C1 MSJMEQRRQOBTRB-UHFFFAOYSA-N 0.000 claims description 4
- OGNZZTLIIQCYCG-UHFFFAOYSA-N N1C=CC=CC=C1.C1=CC=CC=2OC3=C(C21)C=CC=C3 Chemical class N1C=CC=CC=C1.C1=CC=CC=2OC3=C(C21)C=CC=C3 OGNZZTLIIQCYCG-UHFFFAOYSA-N 0.000 claims description 4
- 229910052703 rhodium Inorganic materials 0.000 claims description 4
- JGDDQGALWWRCRZ-UHFFFAOYSA-N C1=CC=CC=2[Se]C3=C(C21)C=CC=C3.N3C=CC=CC=C3 Chemical compound C1=CC=CC=2[Se]C3=C(C21)C=CC=C3.N3C=CC=CC=C3 JGDDQGALWWRCRZ-UHFFFAOYSA-N 0.000 claims description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 3
- 125000003636 chemical group Chemical group 0.000 claims description 3
- 229910052762 osmium Inorganic materials 0.000 claims description 3
- 230000003647 oxidation Effects 0.000 claims description 3
- 238000007254 oxidation reaction Methods 0.000 claims description 3
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims description 2
- OBTVATRSWTWNGS-UHFFFAOYSA-N acetyl 2-oxopropanoate Chemical group CC(=O)OC(=O)C(C)=O OBTVATRSWTWNGS-UHFFFAOYSA-N 0.000 claims description 2
- 230000003190 augmentative effect Effects 0.000 claims description 2
- 230000005611 electricity Effects 0.000 claims description 2
- 229910052737 gold Inorganic materials 0.000 claims description 2
- 229910052702 rhenium Inorganic materials 0.000 claims description 2
- 229910052707 ruthenium Inorganic materials 0.000 claims description 2
- 229910052711 selenium Inorganic materials 0.000 claims description 2
- 239000011669 selenium Substances 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims 1
- 239000010410 layer Substances 0.000 description 92
- 239000000463 material Substances 0.000 description 89
- 0 CC(CC=CC)(C=C1)C=C*(C)=C1c(c(C)c1)ccc1-c1ccccc1 Chemical compound CC(CC=CC)(C=C1)C=C*(C)=C1c(c(C)c1)ccc1-c1ccccc1 0.000 description 74
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 48
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 26
- 239000002019 doping agent Substances 0.000 description 24
- 230000004888 barrier function Effects 0.000 description 18
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- 150000004696 coordination complex Chemical class 0.000 description 13
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 12
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 12
- 150000003384 small molecules Chemical class 0.000 description 12
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 11
- 238000000034 method Methods 0.000 description 11
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 10
- 238000004770 highest occupied molecular orbital Methods 0.000 description 10
- 239000000758 substrate Substances 0.000 description 10
- 230000005540 biological transmission Effects 0.000 description 9
- 150000002240 furans Chemical class 0.000 description 8
- BNRDGHFESOHOBF-UHFFFAOYSA-N 1-benzoselenophene Chemical compound C1=CC=C2[se]C=CC2=C1 BNRDGHFESOHOBF-UHFFFAOYSA-N 0.000 description 7
- 150000003222 pyridines Chemical class 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 6
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 6
- CUFNKYGDVFVPHO-UHFFFAOYSA-N azulene Chemical compound C1=CC=CC2=CC=CC2=C1 CUFNKYGDVFVPHO-UHFFFAOYSA-N 0.000 description 6
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 6
- 239000004305 biphenyl Substances 0.000 description 6
- 235000010290 biphenyl Nutrition 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 230000008859 change Effects 0.000 description 6
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- 230000003111 delayed effect Effects 0.000 description 6
- DHFABSXGNHDNCO-UHFFFAOYSA-N dibenzoselenophene Chemical compound C1=CC=C2C3=CC=CC=C3[se]C2=C1 DHFABSXGNHDNCO-UHFFFAOYSA-N 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
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- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 6
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 6
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- 125000004122 cyclic group Chemical group 0.000 description 5
- 239000012634 fragment Substances 0.000 description 5
- 150000002894 organic compounds Chemical class 0.000 description 5
- 230000027756 respiratory electron transport chain Effects 0.000 description 5
- 238000006467 substitution reaction Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000000151 deposition Methods 0.000 description 4
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 4
- 125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 4
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- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical compound C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 description 4
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- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 3
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- CIKXMSYOZSDGRF-UHFFFAOYSA-N 9,9,10,10-tetramethylanthracene Chemical compound C1=CC=C2C(C)(C)C3=CC=CC=C3C(C)(C)C2=C1 CIKXMSYOZSDGRF-UHFFFAOYSA-N 0.000 description 3
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- MRNHPUHPBOKKQT-UHFFFAOYSA-N indium;tin;hydrate Chemical compound O.[In].[Sn] MRNHPUHPBOKKQT-UHFFFAOYSA-N 0.000 description 2
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- 239000011241 protective layer Substances 0.000 description 2
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 2
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Abstract
The present invention relates to electroluminescent organic material and device.A kind of composition is disclosed, and it includes the first compound, wherein first compound can serve as the emitter in organic light emitting apparatus at room temperature.A kind of phosphorescent emitters compound being used in organic light emitting apparatus is disclosed, wherein described compound has at least one aromatic ring and at least one substituent R, each in wherein described at least one R is directly bonded to one in the aromatic ring, wherein each at least one R has following formula.
Description
The cross reference of related application
The application requires the U.S.Provisional Serial submitted on the 23rd of September in 2016 according to 35U.S.C. § 119 (e) (1)
62/398,638 priority, its content are incorporated herein in a manner of introducing.
Technical field
The present invention relates to the compound for use as phosphorescent emitters；With include its device, such as Organic Light Emitting Diode.More
Exactly, the present invention is shown for manufacturing new phosphorescent emitters to improve the new substituted base of the device efficiency of OLED device
And part.
Background technology
For a variety of reasons, become to be becoming increasingly popular using the electrooptical device of organic material.For manufacturing described device
Many materials it is relatively inexpensive, therefore organic photoelectric device have better than inorganic device cost advantage potentiality.In addition,
The intrinsic property (such as it is flexible) of organic material can make it relatively be applied to application-specific, manufacture such as on flexible substrates.
The example of organic photoelectric device include Organic Light Emitting Diode/device (OLED), organic photoelectric transistor, organic photovoltaic battery and
Organic photodetectors.For OLED, organic material can have the performance advantage better than conventional material.For example, it is organic
The wavelength of emission layer transmitting light generally can be adjusted easily with appropriate dopant.
OLED utilizes organic film, and it can launch light when voltage is put on device.OLED, which just turns into, is used for such as flat board
Increasingly concerned technology in display, illumination and the application of backlight.U.S. Patent No. 5,844,363, the 6,303,238th
Number and the 5th, 707, No. 745 described in some OLED materials and configuration, the patent is incorporated herein in entirety by reference.
One application of phosphorescent emissive molecules is full-color display.Need to be suitable for for the professional standard of this class display
Launch the pixel of particular color (being referred to as " saturation " color).Specifically, these standards need saturated red, green and blue picture
Element.Or OLED can be designed to launch white light.In conventional LCD device, using absorption filter filtering from white
The transmitting of backlight is to produce red, green and blue emission.It is constructed to can be used for OLED.White OLED can be single
EML devices or stacked structure.Color can be measured using CIE coordinates known in art.
One example of green emissive molecule is three (2- phenylpyridines) iridium, is expressed as Ir (ppy)3, it has following knot
Structure：
In figure in this figure and hereafter, we describe the coordinate bond of nitrogen and metal (being Ir herein) with form of straight lines.
As used herein, term " organic " polymeric material and small molecule including can be used for manufacturing organic photoelectric device has
Machine material." small molecule " refers to and any organic material of non-polymer, and " small molecule " may be actually quite big.One
In the case of a little, small molecule can include repeat unit.For example, can't be by a certain point using chain alkyl as substituent
Son removes from " small molecule " classification.Small molecule can also be incorporated in polymer, such as the side joint base on main polymer chain
Group or the part as main chain.Small molecule can function as the core of dendritic, the dendritic
It is made up of a series of chemical shells of structures on core.The core of dendritic can be fluorescence or phosphorescence
Small molecule emitter.Dendritic can be " small molecule ", and think all trees currently used in OLED fields
Dendritic polymer is all small molecule.
As used herein, " top " means farthest from substrate, and " bottom " means near substrate.It is described in first layer
In the case of for " being placed in " second layer " top ", first layer is placed in from substrate remotely.Unless regulation first layer "AND"
The second layer " contact ", otherwise there may be other layers between first and second layer.For example, even if being deposited between negative electrode and anode
In various organic layers, negative electrode can be still described as to " being placed in " anode " top ".
As used herein, " solution can be handled " mean can in the form of solution or suspension in liquid medium dissolving,
Disperse or transmit and/or deposited from liquid medium.
When thinking that part directly facilitates the photo-sensitive characteristic of emissive material, the part can be referred to as " light sensitivity ".
When thinking that part does not facilitate the photo-sensitive characteristic of emissive material, the part can be referred to as " complementary ", but complementary
Part can change the property of photoactive ligand.
As used herein, and such as those skilled in the art generally will be understood that, if the first energy level is closer to vacuum
Energy level, then first " highest occupancy molecular orbit " (Highest Occupied Molecular Orbital, HOMO) or " most
Low vacant molecular orbit " (Lowest Unoccupied Molecular Orbital, LUMO) energy level " being more than " or " being higher than "
2nd HOMO or lumo energy.Due to ionization potential (IP) to be measured as to the negative energy relative to vacuum level, thus it is higher
HOMO energy levels correspond to the IP (IP of less negative (less negative)) with smaller absolute value.Similarly, higher LUMO energy
Level corresponds to the electron affinity (EA) (less negative EA) with smaller absolute value.It is the conventional energy level of vacuum level at top
On figure, the lumo energy of material is higher than the HOMO energy levels of identical material." higher " HOMO or lumo energy are shown as than " relatively low "
HOMO or lumo energy are closer to the top of this figure.
As used herein, and such as those skilled in the art generally will be understood that, if the first work function is with higher
Absolute value, then the first work function " being more than " or " being higher than " second work function.Because it is relative to true generally by power function measuring
The negative of unoccupied level, so this means that " higher " work function is more negative (more negative).It is vacuum level at top
On conventional energy level diagram, " higher " work function is illustrated as in a downward direction from vacuum level farther out.Therefore, HOMO and LUMO energy
The definition of level follows the rule different from work function.
It can be seen in U.S. Patent No. 7,279,704 on OLED and the more details of definition described above, institute
Patent is stated to be incorporated herein in entirety by reference.
The content of the invention
According to an aspect of the present invention, a kind of composition is disclosed, and it includes the first compound.First compound can be
The emitter in OLED is served as at room temperature.First compound includes at least one aromatic ring and at least one substituent R；Wherein
Each at least one R is directly bonded one into aromatic ring；
Each in wherein at least one R has following formula：Wherein L is direct key or had
Machine linking group；Wherein X1And X2It is each independently selected from the group being made up of carbon and silicon；Wherein R1And R2Each represent monosubstituted
To possible the maximum number of substituted or unsubstituted；Wherein R1To R6It is each independently selected from the group consisted of：Hydrogen, deuterium,
Halogen, alkyl, cycloalkyl, miscellaneous alkyl, aralkyl, alkoxy, aryloxy group, amino, silylation, alkenyl, cycloalkenyl group, miscellaneous thiazolinyl,
Alkynyl, aryl, heteroaryl, acyl group, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfenyl (sulfanyl), sulfinyl, sulfonyl, phosphine
Base and its combination；And wherein R3To R6Any neighbouring substituent optionally engage or condense cyclization.
According to a kind of emitting area being in OLED on the other hand, is disclosed, wherein the emitting area includes one kindization
Compound, it includes at least one aromatic ring and at least one substituent R；Each in wherein at least one R is directly bonded
One into aromatic ring；
Each in wherein at least one R has following formula：Wherein L is direct key or had
Machine linking group；Wherein X1And X2It is each independently selected from the group being made up of carbon and silicon；Wherein R1And R2Each represent monosubstituted
To possible the maximum number of substituted or unsubstituted；Wherein R1To R6It is each independently selected from the group consisted of：Hydrogen, deuterium,
Halogen, alkyl, cycloalkyl, miscellaneous alkyl, aralkyl, alkoxy, aryloxy group, amino, silylation, alkenyl, cycloalkenyl group, miscellaneous thiazolinyl,
Alkynyl, aryl, heteroaryl, acyl group, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfenyl, sulfinyl, sulfonyl, phosphino- and its combination；
And wherein R3To R6Any neighbouring substituent optionally engage or condense cyclization.
According on the other hand, a kind of OLED is disclosed, wherein the OLED includes anode；Negative electrode；And organic layer.It is described organic
Layer is placed between anode and negative electrode and comprising the first compound；Wherein described first compound includes at least one aromatic series
Ring and at least one substituent R；Each in wherein at least one R is directly bonded one into aromatic ring；Wherein extremely
Each in a few R has following formula：Wherein L is direct key or organo linking group；Wherein
X1And X2It is each independently selected from the group being made up of carbon and silicon；Wherein R1And R2Each represent and monosubstituted arrive possible maximum number
Purpose is substituted or unsubstituted；Wherein R1To R6It is each independently selected from the group consisted of：Hydrogen, deuterium, halogen, alkyl, cycloalkanes
Base, miscellaneous alkyl, aralkyl, alkoxy, aryloxy group, amino, silylation, alkenyl, cycloalkenyl group, miscellaneous thiazolinyl, alkynyl, aryl, heteroaryl
Base, acyl group, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfenyl, sulfinyl, sulfonyl, phosphino- and its combination；And wherein R3To R6
Any neighbouring substituent optionally engage or condense cyclization.
According on the other hand, a kind of consumer product for including OLED is disclosed, wherein the OLED includes anode；Negative electrode；
And organic layer, wherein the organic layer is placed between anode and negative electrode and comprising the first compound, wherein first chemical combination
Thing includes at least one aromatic ring and at least one substituent R；Each in wherein at least one R is directly bonded to fragrance
One in race's ring；Each in wherein at least one R has following formula as defined herein：
According on the other hand, a kind of composite of inclusion compound is also disclosed, the compound includes at least one fragrance
Race's ring and at least one substituent R；Each in wherein at least one R is directly bonded one into aromatic ring；Wherein
Each at least one R has following formula as defined herein：
Brief description of the drawings
Fig. 1 shows a kind of organic light emitting apparatus.
Inversion type organic light emitting apparatus of Fig. 2 displayings without independent electronic transport layer.
Embodiment
In general, OLED includes at least one organic layer, its be placed between anode and negative electrode and with anode and the moon
Pole electrically connects.When a current is applied, anode injects hole and negative electrode is injected electrons into organic layer.Institute's injected holes and electricity
Son is each towards the electrode transfer of oppositely charged.When electronics and hole position on the same molecule, formed " exciton ", it is tool
There is the localized electron-hole pair for exciting energy state.When exciton is by optical sender relaxation, launch light.In some cases, swash
Son can be positioned on quasi-molecule (excimer) or exciplex.Non-radiative mechanism (such as thermal relaxation) it can also happen that, it is but logical
Often it is considered as undesirable.
Initial OLED uses the emitting molecule from singlet emission light (" fluorescence "), such as such as U.S. Patent No. 4,769,
Disclosed in No. 292, it is incorporated in entirety by reference.Fluorescent emission generally occurs within the time frame less than 10 nanoseconds.
Recently, the OLED with the emissive material from triplet transmitting light (" phosphorescence ") has been illustrated.Ba Erduo
(Baldo) et al., " high efficiency phosphorescent transmitting (the Highly Efficient from Organnic electroluminescent device
Phosphorescent Emission from Organic Electroluminescent Devices) ", it is natural
(Nature), volume 395,151-154,1998 (" Ba Erduo-I ")；With Ba Erduo et al., " based on the extremely efficient of electroluminescent phosphorescence
Green organic light emitting apparatus (Very high-efficiency green organic light-emitting devices
Based on electrophosphorescence) ", Applied Physics bulletin (Appl.Phys.Lett.), volume 75,3,4-
6 phases (1999) (" Ba Erduo-II "), the document is incorporated in entirety by reference.No. 7,279,704 5- of U.S. Patent No.
Phosphorescence is more fully described in 6 columns, the patent is herein incorporated by reference.
Fig. 1 shows organic light emitting apparatus 100.Figure is not drawn necessarily to scale.Device 100 can include substrate 110, anode
115th, hole injection layer 120, hole transmission layer 125, electronic barrier layer 130, emission layer 135, hole blocking layer 140, electronics pass
Defeated layer 145, electron injecting layer 150, protective layer 155, negative electrode 160 and barrier layer 170.Negative electrode 160 is that have the first conductive layer 162
With the composite cathode of the second conductive layer 164.Device 100 can be manufactured by depositing the layer in order.These various layers and
The property and function of example materials are more fully described in the 6-10 columns of US 7,279,704, and the patent is by reference
It is incorporated to.
More examples of each in these layers can be obtained.For example, flexible and transparent substrate-anode group
Conjunction is disclosed in U.S. Patent No. 5,844,363, and the patent is incorporated in entirety by reference.Hole through p doping passes
The example of defeated layer is with 50:1 mol ratio is doped with F4- TCNQ m-MTDATA, such as U.S. Patent Application Publication No. 2003/
Disclosed in No. 0230980, the patent is incorporated in entirety by reference.Luminous and material of main part example is disclosed in Tang Pu
In the U.S. Patent No. 6,303,238 of gloomy (Thompson) et al., the patent is incorporated in entirety by reference.Mixed through n
The example of miscellaneous electron transfer layer is with 1:1 mol ratio doped with Li BPhen, such as U.S. Patent Application Publication No. 2003/
Disclosed in No. 0230980, the publication is incorporated in entirety by reference.The U.S. being incorporated in entirety by reference is special
Sharp 5th, 703, No. 436 and the 5th, 707, No. 745 example for disclosing negative electrode, the negative electrode include having containing overlying it is transparent,
Metal (such as Mg of conductive, sputter deposition ITO layer:Ag) the composite cathode of thin layer.The theory on barrier layer and use are in more detail
It is described in U.S. Patent No. 6,097,147 and U.S. Patent Application Publication No. 2003/0230980, the patent is with complete
The mode that text is quoted is incorporated to.The example of implanted layer is provided in U.S. Patent Application Publication No. 2004/0174116, and it is with complete
The mode that text is quoted is incorporated to.The description of protective layer can be seen in U.S. Patent Application Publication No. 2004/0174116, its with
The mode being cited in full text is incorporated to.
Fig. 2 displaying inversion types OLED 200.Described device includes substrate 210, negative electrode 215, emission layer 220, hole transport
Layer 225 and anode 230.Device 200 can be manufactured by depositing the layer in order.Because most common OLED configurations have peace
The negative electrode being placed in above anode, and device 200 has and is placed in negative electrode 215 under anode 230, so device 200 can be by
Referred to as " inversion type " OLED.Can be in the respective layer of device 200 using similar with those materials described in device 100
Material.Fig. 2 provides the example that some layers how can be saved from the structure of device 100.
Illustrated simple hierarchy is provided by means of non-limiting examples in Fig. 1 and 2, and should be understood that the present invention's
Embodiment can be used in combination with various other structures.It is exemplary on described specific material and structural nature, and
Other materials and structure can be used.Feature OLED can be obtained by combining described various layers by different way, or
Design, performance and cost factor can be based on and omit each layer completely.The other layers not specifically described can also be included.It can use
Material in addition to the material of specific descriptions.Although various layers are described as including single material by many examples presented herein
Material, it should be appreciated that the combination of material, such as main body and the mixture of dopant, or more generally, mixture can be used.This
Outside, the layer can have each Seed Layer.The title for giving various layers herein is not intended with strict restricted.Citing comes
Say, in device 200, the transporting holes of hole transmission layer 225 and inject holes into emission layer 220, and can be retouched
State as hole transmission layer or hole injection layer.In one embodiment, OLED can be described as having and is placed in negative electrode and sun
" organic layer " between pole.This organic layer can include single layer, or further can include as example on Fig. 1 and 2 institutes
The multiple layers for the different organic materials stated.
The structure and material not specifically described, such as the OLED (PLED) comprising polymeric material can also be used, such as not
Disclosed in Lan De (Friend) et al. U.S. Patent No. 5,247,190, the patent is incorporated in entirety by reference.
By means of another example, the OLED with single organic layer can be used.OLED can be stacked, such as to be cited in full text
Described in the U.S. Patent No. 5,707,745 of the welfare that mode is incorporated to this special (Forrest) et al..OLED structure can deviate
Illustrated simple hierarchy in Fig. 1 and 2.For example, substrate can include angled reflecting surface to improve out coupling
(out-coupling), such as the mesa structure such as described in the U.S. Patent No. 6,091,195 of welfare this top grade people,
And/or the concave point structure such as described in the U.S. Patent No. 5,834,893 of boolean's dimension gram (Bulovic) et al., it is described special
Profit is incorporated in entirety by reference.
Unless specified otherwise herein, otherwise any in the layer of each embodiment can be deposited by any suitable method
It is individual.For organic layer, method for optimizing include thermal evaporation, ink-jet (such as the U.S. Patent No. 6 that is incorporated in entirety by reference,
Described in No. 013,982 and No. 6,087,196), organic vapor phase deposition (OVPD) (such as the good fortune that is incorporated in entirety by reference
Described in the U.S. Patent No. 6,337,102 of sharp this top grade people) and the deposition of (OVJP) printed (such as by organic vapor jet
Described in the U.S. Patent No. being incorporated in entirety by reference 7,431,968).Other suitable deposition process include spin coating
With other techniques based on solution.Technique based on solution is preferably carried out in nitrogen or inert atmosphere.For other layers, preferably
Method include thermal evaporation.Preferable patterning method includes the deposition by mask, cold welding (such as in entirety by reference simultaneously
Described in the U.S. Patent No. entered No. 6,294,398 and No. 6,468,819) and with the deposition process of such as ink-jet and OVJP
The associated patterning of certain methods.Other methods can also be used.Can be by material modification to be deposited so that itself and tool
Body deposition process matches.For example, side chain or non-branched and preferably comprise at least three carbon can be used in small molecule
Such as alkyl and aryl substituent come strengthen its be subjected to solution processing ability.Can use has 20 or more carbon
Substituent, and 3 to 20 carbon are preferred scopes.Material with dissymmetrical structure can be than the material with symmetrical structure
With more preferable solution processability, because asymmetric material may have lower recrystallization tendentiousness.Branch can be used
Shaped polymer substituent come strengthen small molecule be subjected to solution processing ability.
The device manufactured according to embodiments of the present invention can optionally further include barrier layer.One purposes on barrier layer
It is the infringement of guard electrode and organic layer from the harmful substance in the environment including moisture, steam and/or gas etc..
Barrier layer can be deposited on substrate, on electrode, be deposited under substrate, electrode or be deposited on substrate, by electrode, or be deposited on device
Any other part (including edge) on.Barrier layer can include single layer or multiple layers.Barrier layer can by it is various
The chemical vapour deposition technique known is formed, and can include the composition with single-phase and the composition with multiple phases.
Any suitable material or combination of materials may be used to barrier layer.Barrier layer and can have inorganic compound or organic compound
Thing or both.Preferable barrier layer includes the mixture of polymeric material and non-cohesive material, is such as incorporated in entirety by reference
U.S. Patent No. 7,968,146, PCT Patent Application the PCT/US2007/023098th and PCT/US2009/ herein
Described in No. 042829.In order to be considered as " mixture ", the aforementioned polymeric materials and non-cohesive material Ying Xiang on barrier layer are formed
Deposit and/or deposit simultaneously with reaction condition.The weight of polymeric material and non-cohesive material ratio can be 95:5 to 5:95 models
In enclosing.Polymeric material and non-cohesive material can be produced by same precursor material.In an example, polymeric material with it is non-polymeric
The mixture of material is substantially made up of polymerization silicon and inorganic silicon.
It is (or single that the device manufactured according to an embodiment of the invention can be incorporated into diversified electronic component module
Member) in, the electronic component module can be incorporated into a variety of electronic products or intermediate module.The electronic product or middle groups
The example of part include can by display screen that end user product manufacturer utilizes, lighting device (such as discrete light source device or
Illumination panel) etc..The electronic component module can optionally include drive electronics and/or power supply.According to the present invention's
Embodiment and the device that manufactures can be incorporated into diversified consumer product, the consumer product has one or more
Individual electronic component module (or unit) is incorporated into wherein.A kind of consumer product for including OLED is disclosed, and the OLED is in OLED
In organic layer include the compounds of this invention.The consumer product should include containing one or more light sources and/or certain species
Any kind of product of one or more of the visual displays of type.Some examples of the consumer product include flat board
Display, computer monitor, medical monitors, television set, billboard, for it is internal or external illumination and/or signalling
It is lamp, head-up display, all-transparent or partially transparent display, flexible display, laser printer, phone, mobile phone, flat
Plate computer, flat board mobile phone, personal digital assistant (PDA), wearable device, laptop computer, digital camera, video camera,
View finder, miniscope (diagonal is less than 2 inches of display), 3-D displays, virtual reality or augmented reality are shown
Device, the vehicles, video wall, theater or the stadium screen for including multiple displays to tile together, and direction board.Can be with
The device manufactured according to the present invention, including passive matrix and active matrix are controlled using various controlling mechanisms.It is intended to institute
The many devices stated in device are used for for the mankind in comfortable temperature range, such as 18 degrees Celsius to 30 degrees Celsius, and
(20-25 degrees Celsius) more preferably at room temperature, but can be outside this temperature range (such as -40 degrees Celsius to+80 degrees Celsius)
Use.
Material described herein and structure can apply in device in addition to oled.For example, such as organic sun
Other electrooptical devices of energy battery and organic photodetectors can use the material and structure.More generally, as organic
The organic device of transistor can use the material and structure.
As used herein, term " halogen ", " halogen " or " halogen " includes fluorine, chlorine, bromine and iodine.
As used herein, term " alkyl " covers straight chain and branched alkyl.Preferable alkyl is containing one to ten five carbon
The alkyl of atom, and including methyl, ethyl, propyl group, 1- Methylethyls, butyl, 1- methyl-propyls, 2- methyl-propyls, amyl group,
1- methyl butyls, 2- methyl butyls, 3- methyl butyls, 1,1- dimethyl propyls, 1,2- dimethyl propyls, 2,2- dimethyl propyls
Deng.In addition, alkyl can be optionally substituted.
As used herein, term " cycloalkyl " covers cyclic alkyl.Preferable cycloalkyl is to contain 3 to 10 ring carbon atoms
Cycloalkyl, and including cyclopropyl, cyclopenta, cyclohexyl, adamantyl etc..In addition, cycloalkyl can optionally be taken
Generation.
As used herein, term " alkenyl " covers straight chain and branched-chain alkenyl.Preferable alkenyl is containing two to ten five carbon
The alkenyl of atom.In addition, alkenyl can be optionally substituted.
As used herein, term " alkynyl " covers straight chain and branch alkynyl.Preferable alkynyl is containing two to ten five carbon
The alkynyl of atom.In addition, alkynyl can be optionally substituted.
As used herein, term " aralkyl " or " aryl alkyl " are interchangeably used and covered with aromatic group
Alkyl as substituent.In addition, aralkyl can be optionally substituted.
As used herein, term " heterocyclic radical " covers aromatic series and non-aromatic cyclic group.Aromatic heterocycle is also anticipated
Refer to heteroaryl.Preferable non aromatic heterocyclyl be containing the heterocyclic radical for including at least one heteroatomic 3 to 7 annular atoms,
And including cyclammonium, such as morpholinyl, piperidyl, pyrrolidinyl, and cyclic ethers, such as tetrahydrofuran, oxinane.It is in addition, miscellaneous
Ring group can be optionally substituted.
As used herein, term " aryl " or " aromatic group " cover monocyclic groups and multi-loop system.It is polycyclic to have
There is two of which carbon for two or more shared rings of two adjacent rings (ring is " fusion "), wherein in the ring
At least one is aromatic, such as other rings can be cycloalkyl, cycloalkenyl group, aryl, heterocycle and/or heteroaryl.Preferably
Aryl be containing six to three ten carbon atoms, preferably six to two ten carbon atoms, more preferably six to ten two carbon atoms aryl.
Especially preferably there is the aryl of six carbon, ten carbon or 12 carbon.Suitable aryl include phenyl, biphenyl, terphenyl,
Triphenylene, four sub- benzene, naphthalene, En, Fu, phenanthrene, fluorenes, pyrene,And Azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorenes and naphthalene.
In addition, aryl can be optionally substituted.
As used herein, term " heteroaryl ", which is covered, can include one to five heteroatomic monocyclic heteroaromatic groups.
It is two adjacent rings (ring is " fusion ") shared two or more that term heteroaryl, which is also included with two of which atom,
The polycyclic heteroaromatic systems of multiple rings, wherein at least one in the ring is heteroaryl, such as other rings can be cycloalkanes
Base, cycloalkenyl group, aryl, heterocycle and/or heteroaryl.Preferable heteroaryl is containing three to three ten carbon atoms, preferably three to two
The heteroaryl of ten carbon atoms, more preferably three to ten two carbon atoms.Suitable heteroaryl includes dibenzothiophenes, dibenzo furan
Mutter, dibenzo selenophen, furans, thiophene, benzofuran, benzothiophene, benzo selenophen, carbazole, indolocarbazole, pyridine radicals Yin
Diindyl, the pyridine of pyrrolo- two, pyrazoles, imidazoles, triazole, oxazole, thiazole, oxadiazoles, dislike triazole, dioxazole, thiadiazoles, pyridine, rattle away
Piperazine, pyrimidine, pyrazine, triazine, oxazines, evil thiazine, oxadiazines, indoles, benzimidazole, indazole, indolizine, benzoxazoles, benzo
Isoxazole, benzothiazole, quinoline, isoquinolin, cinnolines, quinazoline, quinoxaline, naphthyridines, phthalazines, pyridine of talking endlessly, xanthene
(xanthene), acridine, azophenlyene, phenthazine, phenoxazine, benzofuran and pyridine, furans and two pyridines, benzothiophene and pyrrole
Pyridine, the pyridine of thieno two, benzo selenophen and pyridine and selenophen and two pyridines, preferably dibenzothiophenes, dibenzofurans, dibenzo
Selenophen, carbazole, indolocarbazole, imidazoles, pyridine, triazine, benzimidazole, 1,2- azepines borine, 1,3- azepines borine, 1,4- nitrogen
Miscellaneous borine, boron nitrogen alkynes and its aza analogues.In addition, heteroaryl can be optionally substituted.
Alkyl, cycloalkyl, alkenyl, alkynyl, aralkyl, heterocyclic radical, aryl and heteroaryl can be unsubstituted or can be by one
Or multiple substituent substitutions selected from the group consisted of：Deuterium, halogen, alkyl, cycloalkyl, miscellaneous alkyl, aralkyl, alcoxyl
Base, aryloxy group, amino, ring type amidogen, silylation, alkenyl, cycloalkenyl group, miscellaneous thiazolinyl, alkynyl, aryl, heteroaryl, acyl group, carbonyl, carboxylic
Acid, ether, ester, nitrile, isonitrile, sulfenyl, sulfinyl, sulfonyl, phosphino- and its combination.
As used herein, substituent bond of " substituted " expression in addition to H arrives relevant position, such as carbon.Therefore, illustrate
For, in R1When being mono-substituted, then a R1Must not be H.Similarly, in R1During by two substitutions, then two R1Must not be H.
Similarly, in R1When unsubstituted, R1All it is hydrogen for all available positions.
" azepine " title in fragment as described herein, i.e. azepine-dibenzofurans, azepine-dibenzothiophenes etc. means
One or more of C-H groups in each fragment can be replaced by nitrogen-atoms, such as and property without any restrictions, azepine three
Sub- benzene covers dibenzo [f, h] quinoxaline and dibenzo [f, h] quinoline.One of ordinary skill in the art can be easily pre-
Think other nitrogen analogs of azepine-derivative described above, and all such analogs are intended to by as set forth herein
Term cover.
It should be understood that when molecule fragment to be described as substituent or be alternatively attached to another part, its title can be as
It is fragment (such as phenyl, phenylene, naphthyl, dibenzofuran group) it is general or as its be whole molecule (such as benzene, naphthalene,
Dibenzofurans) typically writing.As used herein, the mode of these different name substituents or junction fragment is considered as equivalent
's.
According to an aspect of the present invention, a kind of composition is disclosed, and it includes the first compound.First compound can be
The emitter in organic light emitting apparatus is served as at room temperature.First compound has at least one aromatic ring and at least one substitution
Base R；Each in wherein at least one R is directly bonded one into aromatic ring；
Each in wherein at least one R has following formula：Wherein L is direct key or had
Machine linking group；Wherein X1And X2It is each independently selected from the group being made up of carbon and silicon；Wherein R1And R2Each represent monosubstituted
To possible the maximum number of substituted or unsubstituted；Wherein R1To R6It is each independently selected from the group consisted of：Hydrogen, deuterium,
Halogen, alkyl, cycloalkyl, miscellaneous alkyl, aralkyl, alkoxy, aryloxy group, amino, silylation, alkenyl, cycloalkenyl group, miscellaneous thiazolinyl,
Alkynyl, aryl, heteroaryl, acyl group, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfenyl, sulfinyl, sulfonyl, phosphino- and its combination；
And wherein R3To R6Any neighbouring substituent optionally engage or condense cyclization.
In some embodiments of composition, L is direct key.
In some embodiments of composition, L is the organo linking group selected from the group consisted of：Aryl, quilt
Substituted aryl, heteroaryl, substituted heteroaryl and its combination.
In some embodiments of composition, X1And X2For carbon.
In some embodiments of composition, X1For carbon and X2For silicon.
In some embodiments of composition, R3To R6It is each independently selected from the group consisted of：Alkyl, cycloalkanes
Base, its partly or completely variant of perdeuterated, its partly or completely variant of perfluorinate and its combination.
In some embodiments of composition, the first compound can serve as the phosphorescence in organic light emitting apparatus at room temperature
Emitter.
In some embodiments of composition, the first compound can serve as the fluorescence in organic light emitting apparatus at room temperature
Emitter.
In some embodiments of composition, the first compound can serve as the delay in organic light emitting apparatus at room temperature
Fluorescent emitter.
In some embodiments of composition, the first compound can be at room temperature from triplet excited state to single ground state emission
Light.
In some embodiments of composition, the first compound is the metal coordination complex for having metal-carbon key.
In some embodiments of composition, metal is selected from the group consisted of：Ir、Rh、Re、Ru、Os、Pt、Au
And Cu.
In some embodiments of composition, metal is Ir or Pt.In certain embodiments, metal is Ir.In some realities
Apply in example, metal is Pt.
In some embodiments of composition, each at least one R is independently selected from the group consisted of：
In some embodiments of composition, the first compound has formula M (L1)x(L2)y(L3)z；
Wherein L1、L2And L3Can be with identical or different；
Wherein L1、L2And L3In it is at least one be not acetyl pyruvate part；
Wherein x is 1,2 or 3；
Wherein y is 0,1 or 2；
Wherein z is 0,1 or 2；
Wherein x+y+z is metal M oxidation state；
Wherein L1、L2And L3It is each independently selected from the group consisted of：
Wherein each X1To X17Independently selected from the group being made up of carbon and nitrogen；
Wherein X is selected from the group consisted of：BR', NR', PR', O, S, Se, C=O, S=O, SO2、CR'R”、SiR'
R " and GeR'R "；
Wherein R' and R " is optionally condensed or engaged to form ring；
Wherein each Ra、Rb、RcAnd RdIt can represent monosubstituted to possible the maximum number of substituted or unsubstituted；
Wherein R', R ", Ra、Rb、RcAnd RdIt is each independently selected from the group consisted of：Hydrogen, deuterium, halogen, alkyl,
Cycloalkyl, miscellaneous alkyl, aralkyl, alkoxy, aryloxy group, amino, silylation, alkenyl, cycloalkenyl group, miscellaneous thiazolinyl, alkynyl, aryl,
Heteroaryl, acyl group, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfenyl, sulfinyl, sulfonyl, phosphino- and its combination；And
Wherein Ra、Rb、RcAnd RdAny two optionally condense or engage adjacent to substituent and multiple tooth matched somebody with somebody with forming ring or being formed
Body；And
Wherein described Ra、Rb、RcAnd RdIn it is at least one including at least one R.
In some embodiments of composition, the first compound has Formulas I r (L1)2(L2), wherein L1And L2As determined above
Justice.
The first compound has Formulas I r (L wherein1)2(L2) composition some embodiments in, L1With selected from by with
The formula of the group of lower composition：
And
Wherein L2With following formula：
In certain embodiments, L2With following formula：
Wherein Re、Rf、RhAnd RiIndependently selected from the group consisted of：Alkyl, cycloalkyl, aryl and heteroaryl；
Wherein Re、Rf、RhAnd RiIn at least one there are at least two carbon atoms；
Wherein RgSelected from the group consisted of：Hydrogen, deuterium, halogen, alkyl, cycloalkyl, miscellaneous alkyl, aralkyl, alcoxyl
Base, aryloxy group, amino, silylation, alkenyl, cycloalkenyl group, miscellaneous thiazolinyl, alkynyl, aryl, heteroaryl, acyl group, carbonyl, carboxylic acid, ester,
Nitrile, isonitrile, sulfenyl, sulfinyl, sulfonyl, phosphino- and its combination.
The first compound has Formulas I r (L wherein1)2(L2) composition some embodiments in, L1And L2It is different and
It is each independently selected from the group consisted of：
The first compound has Formulas I r (L wherein1)2(L2) composition some embodiments in, L1And L2It is each independent
Ground is selected from the group consisted of：
The first compound has formula M (L as defined above wherein1)x(L2)y(L3)zComposition some implementation
In example, the first compound has formula Pt (L1)2Or Pt (L1)(L2).The first compound has formula Pt (L wherein1)2Or Pt (L1)
(L2) some embodiments in, L1With another L1Or and L2Connection forms tetradentate ligandses.
The first compound has formula M (L as defined above wherein1)x(L2)y(L3)zComposition some implementation
In example, Ra、Rb、RcAnd RdIn at least one include CD, CD including alkyl or cycloalkyl, the alkyl or cycloalkyl2Or CD3,
Wherein D is deuterium.
In some embodiments of composition, the first compound has formula M (L1)x(L2)y(L3)z, L1、L2And L3In extremely
Few one selected from the group consisted of：
In a certain embodiment of composition, wherein the first compound has formula M (L1)x(L2)y(L3)z, L1、L2And L3In
It is at least one selected from the group consisted of：
In a certain embodiment of composition, wherein the first compound has formula M (L1)x(L2)y(L3)z, L1、L2And L3In
It is at least one selected from the group being made up of ligand 1 to ligand 1 35, the compound is with Formulas I r (part i) (LBj)2Change
Compound x；
Wherein x=300i+j-300；I is 1 to 135 integer, and j is 1 to 300 integer；And wherein LB1Arrive
LB300With following structure：
According on the other hand, a kind of composite for including compound described herein is disclosed.
According to another aspect of the present invention, a kind of OLED is disclosed.The OLED is included：Anode；Negative electrode；And organic layer, its
It is placed between anode and negative electrode, includes the first compound；Wherein described first compound can serve as organic hair at room temperature
Emitter in electro-optical device；Wherein described first compound has at least one aromatic ring and at least one substituent R；Wherein
Each at least one R is directly bonded one into aromatic ring；Under each in wherein at least one R has
Formula：
Wherein L is direct key or organo linking group；
Wherein X1And X2It is each independently selected from the group being made up of carbon and silicon；
Wherein R1And R2Each represent monosubstituted to possible the maximum number of substituted or unsubstituted；
Wherein R1To R6It is each independently selected from the group consisted of：Hydrogen, deuterium, halogen, alkyl, cycloalkyl, miscellaneous alkane
Base, aralkyl, alkoxy, aryloxy group, amino, silylation, alkenyl, cycloalkenyl group, miscellaneous thiazolinyl, alkynyl, aryl, heteroaryl, acyl group,
Carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfenyl, sulfinyl, sulfonyl, phosphino- and its combination；And
Wherein R3To R6Any neighbouring substituent optionally engage or condense cyclization.
In OLED some embodiments, the organic layer is emission layer, and the compound be transmitting dopant or
Non-emissive dopant.Dopant whether by emission type by depending on the special body compound utilized in emission layer.
In OLED some embodiments, the organic layer further includes main body, wherein the main body contains benzene
And the triphenylene of fused thiophene or benzo-fused furans；Any substituent in wherein described main body is independently selected from by following
The non-condensed substituent of the group of composition：CnH2n+1、OCnH2n+1、OAr1、N(CnH2n+1)2、N(Ar1)(Ar2), CH=CH-
CnH2n+1、C≡CCnH2n+1、Ar1、Ar1-Ar2、CnH2n-Ar1It is or unsubstituted；
Wherein n is 1 to 10；And
Wherein Ar1And Ar2Independently selected from the group consisted of：Benzene, biphenyl, naphthalene, triphenylene, carbazole and its heteroaryl
Fragrant race's analog.
In OLED some embodiments, the organic layer further includes main body, and wherein main body includes at least one choosing
From the chemical group of the group consisted of：Triphenylene, carbazole, dibenzothiophenes, dibenzofurans, dibenzo selenophen, nitrogen
Miscellaneous-triphenylene, azepine carbazole, azepine-dibenzothiophenes, azepine-dibenzofurans and azepine-dibenzo selenophen.
In OLED some embodiments, the organic layer further includes main body, wherein the main body is selected from by following
The group of composition：
With its combination.
In OLED some embodiments, the organic layer further includes main body, wherein the main body includes metal network
Compound.
In certain embodiments, the OLED has one or more features selected from the group consisted of：Flexible,
Rollable, foldable, stretchable and bending.In certain embodiments, the OLED is transparent or semitransparent.In some implementations
In example, the OLED further includes the layer of CNT.
In certain embodiments, the OLED further includes the layer of delayed fluorescence emitter.In some embodiments
In, the OLED includes rgb pixel arrangement or white variegates optical filter pixel arrangement.In certain embodiments, the OLED
It is mobile device, handheld apparatus or wearable device.In certain embodiments, the OLED be diagonal be less than 10 inches or
Area is less than 50 square inches of display panel.In certain embodiments, the OLED is that diagonal is at least 10 inches or face
The display panel that product is at least 50 square inches.In certain embodiments, the OLED is illumination panel.
In certain embodiments, the OLED has one or more features selected from the group consisted of：Flexible,
Rollable, foldable, stretchable and bending.In certain embodiments, the OLED is transparent or semitransparent.In some implementations
In example, the OLED further includes the layer of CNT.
In certain embodiments, the OLED further includes the layer of delayed fluorescence emitter.In some embodiments
In, the OLED includes rgb pixel arrangement or white variegates optical filter pixel arrangement.In certain embodiments, the OLED
It is mobile device, handheld apparatus or wearable device.In certain embodiments, the OLED be diagonal be less than 10 inches or
Area is less than 50 square inches of display panel.In certain embodiments, the OLED is that diagonal is at least 10 inches or face
The display panel that product is at least 50 square inches.In certain embodiments, the OLED is illumination panel.
According to an aspect of the present invention, a kind of emitting area being in organic light emitting apparatus is disclosed.Emitting area includes
First compound, wherein first compound can serve as the emitter in organic light emitting apparatus at room temperature, wherein described
First compound includes at least one aromatic ring and at least one substituent；Each direct key in wherein at least one R
Tie one in aromatic ring；Each in wherein at least one R has following formula：
Wherein L is direct key or organo linking group；
Wherein X1And X2It is each independently selected from the group being made up of carbon and silicon；
Wherein R1And R2Each represent monosubstituted to possible the maximum number of substituted or unsubstituted；
Wherein R1To R6It is each independently selected from the group consisted of：Hydrogen, deuterium, halogen, alkyl, cycloalkyl, miscellaneous alkane
Base, aralkyl, alkoxy, aryloxy group, amino, silylation, alkenyl, cycloalkenyl group, miscellaneous thiazolinyl, alkynyl, aryl, heteroaryl, acyl group,
Carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfenyl, sulfinyl, sulfonyl, phosphino- and its combination；And
Wherein R3To R6Any neighbouring substituent optionally engage or condense cyclization.
In some embodiments of emitting area, the compound is transmitting dopant or non-emissive dopant.
In some embodiments of emitting area, the emitting area further includes main body, wherein the main body includes
At least one metal complex selected from the group consisted of：Triphenylene, carbazole, dibenzothiophenes, dibenzofurans, two
Benzo selenophen, azepine-triphenylene, azepine-carbazole, azepine-dibenzothiophenes, azepine-dibenzofurans and azepine-dibenzo selenium
Fen.
In some embodiments of emitting area, the emitting area further includes main body, wherein the main body is selected from
The group consisted of：
With its combination.
According to another aspect of the present invention, a kind of consumer product for including OLED is disclosed, and the OLED is in OLED
Organic layer includes the first compound of the invention.
In certain embodiments, the compound can be transmitting dopant.In certain embodiments, the compound can
To be eliminated via phosphorescence, fluorescence, hot activation delayed fluorescence (i.e. TADF, also referred to as E types delayed fluorescence), triplet-triplet or
The combination of these techniques produces transmitting.
According on the other hand, a kind of composite for including compound described herein is also disclosed.
OLED disclosed herein can be incorporated into one kind in consumer product, electronic component module and illumination panel or
In a variety of.Organic layer can be emission layer, and compound can be transmitting dopant in certain embodiments, and compound exists
It can be non-emissive dopant in other embodiments.
The organic layer can also include main body.In certain embodiments, two or more main bodys are preferable.One
In a little embodiments, main body used can play minimum a) bipolar, b in electric charge transmission) electric transmission, c) hole biography
It is defeated, or d) wide bandgap material.In certain embodiments, main body can include metal complex.Main body can be thick containing benzo
Close the triphenylene of thiophene or benzo-fused furans.Any substituent in main body can be independently selected from the group consisted of
The non-condensed substituent of group：CnH2n+1、OCnH2n+1、OAr1、N(CnH2n+1)2、N(Ar1)(Ar2), CH=CH-CnH2n+1、C≡C-
CnH2n+1、Ar1、Ar1-Ar2And CnH2n-Ar1, or main body is unsubstituted.In foregoing substituents, n can be in the range of 1 to 10；And
And Ar1And Ar2Can be independently selected from the group consisted of：Benzene, biphenyl, naphthalene, triphenylene, carbazole and its heteroaromatic class
Like thing.Main body can be inorganic compound.For example, the inorganic material containing Zn, such as ZnS.
Main body can include the compound of at least one chemical group selected from the group consisted of：Triphenylene,
Carbazole, dibenzothiophenes, dibenzofurans, dibenzo selenophen, azepine triphenylene, azepine carbazole, azepine-dibenzothiophenes, nitrogen
Miscellaneous-dibenzofurans and azepine-dibenzo selenophen.Main body can include metal complex.Main body can be (but are not limited to) selecting
From the specific compound of the group consisted of：
With its combination.Extraneous information presented below on possible main body.
In still yet another aspect of the present, a kind of composite for including compounds disclosed herein is described.Allotment
Thing can include one or more components disclosed herein selected from the group consisted of：Solvent, main body, hole injection
Material, hole mobile material and electron transport layer materials.
With the combination of other materials
Here depicted as the certain layer suitable for organic light emitting apparatus material can with it is a variety of present in device
Other materials are applied in combination.For example, it is disclosed herein transmitting dopant can with it is that may be present extensively a variety of main bodys,
Transport layer, barrier layer, implanted layer, electrode and other layers of combined use.The material for being described below or referring to is can be with this paper institutes
The non-limiting examples for the material that disclosed compound is applied in combination, and those skilled in the art can easily consult
Document is to differentiate the other materials that can be applied in combination.
Conductivity dopants：
Charge transport layer can be doped with conductivity dopants generally to change its charge carrier density, and this transfers to change
Become its electric conductivity.Electric conductivity is increased by generating charge carrier in host material, and depending on the type of dopant, is gone back
The change of the fermi level (Fermi level) of semiconductor can be realized.Hole transmission layer can adulterate doped with p-type conductivity
Agent, and n-type conductivity dopant is used in electron transfer layer.
Can with combination of materials disclosed herein be used for OLED in conductivity dopants non-limiting examples with
Disclose those materials bibliography illustrate together it is as follows：EP01617493、EP01968131、EP2020694、EP2684932、
US20050139810、US20070160905、US20090167167、US2010288362、WO06081780、
WO2009003455、WO2009008277、WO2009011327、WO2014009310、US2007252140、US2015060804
And US2012146012.
HIL/HTL：
Hole injection/transmission material used is not particularly limited in the present invention, and can use any compound, only
Compound is wanted to be typically used as hole injection/transmission material.The example of material includes but is not limited to：Phthalocyanine or porphyrin derive
Thing；Aromatic amine derivative；Indolocarbazole derivatives；Polymer containing fluorohydrocarbon；The polymer of conductive dopant；
Conducting polymer, such as PEDOT/PSS；The self assembly monomer of the derivative compound of phosphonic acids and silane derivative freely；Metal aoxidizes
Thing derivative, such as MoOx；P-type semiconducting organic compounds, such as Isosorbide-5-Nitrae, 5,8,9,12- six azepine triphenylene pregnancy nitriles；Metal network
Compound；And crosslinkable.
Example for HIL or HTL aromatic amine derivative includes but is not limited to following general structure：
Ar1To Ar9In each be selected from：The group being made up of aromatic hydrocarbon cyclic compound, such as benzene, biphenyl, connection three
Benzene, triphenylene, naphthalene, En, Fu, phenanthrene, fluorenes, pyrene,And Azulene；The group being made up of aromatic heterocyclic compounds, such as dibenzo thiophene
Fen, dibenzofurans, dibenzo selenophen, furans, thiophene, benzofuran, benzothiophene, benzo selenophen, carbazole, indoles and click
Azoles, pyridine radicals indoles, the pyridine of pyrrolo- two, pyrazoles, imidazoles, triazole, oxazole, thiazole, oxadiazoles, evil triazole, dioxazole, thiophene two
Azoles, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazines, evil thiazine, oxadiazines, indoles, benzimidazole, indazole, indolizine, benzo
Oxazole, benzo isoxazole, benzothiazole, quinoline, isoquinolin, cinnolines, quinazoline, quinoxaline, naphthyridines, phthalazines, pyridine of talking endlessly, oxa-
Anthracene, acridine, azophenlyene, phenthazine, phenoxazine, benzofuran and pyridine, furans and two pyridines, benzothiophene and pyridine, thieno
Two pyridines, benzo selenophen and pyridine and selenophen and two pyridines；And the group being made up of 2 to 10 cyclic structural units, it is described
Cyclic structural unit is selected from aromatic cyclic hydrocarbon group and the same type of aromatic heterocycle or different types of group and straight
Connect or via in oxygen atom, nitrogen-atoms, sulphur atom, silicon atom, phosphorus atoms, boron atom, chain structure unit and aliphatic ring group
It is at least one to be bonded each other.Each Ar can be substituted with the substituent of group that is unsubstituted or being chosen consist of certainly：
Deuterium, halogen, alkyl, cycloalkyl, miscellaneous alkyl, aralkyl, alkoxy, aryloxy group, amino, silylation, alkenyl, cycloalkenyl group, miscellaneous alkene
Base, alkynyl, aryl, heteroaryl, acyl group, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfenyl, sulfinyl, sulfonyl, phosphino- and its group
Close.
In an aspect, Ar1To Ar9Independently selected from the group consisted of：
Wherein k is 1 to 20 integer；X101To X108It is C (including CH) or N；Z101It is NAr1, O or S；Ar1With institute above
The identical group of definition.
The example of metal complex used includes but is not limited to below general formula in HIL or HTL：
Wherein Met is the metal that atomic weight can be more than 40；(Y101-Y102) it is bidentate ligand, Y101And Y102Independently select
From C, N, O, P and S；L101It is assistant ligand；K' is 1 integer value for arriving the maximum part number that can be connected with metal；And k'+
K " is the maximum part number that can be connected with metal.
In an aspect, (Y101-Y102) it is 2- phenylpyridine derivatives.In another aspect, (Y101-Y102) it is carbene
Part.In another aspect, Met is selected from Ir, Pt, Os and Zn.In another aspect, metal complex has compared to Fc+/Fc
Minimum oxidation potential in the solution less than about 0.6V of coupling.
Can with combination of materials disclosed herein be used for OLED in HIL and HTL material non-limiting examples with
Disclose those materials bibliography illustrate together it is as follows：CN102702075、DE102012005215、EP01624500、
EP01698613、EP01806334、EP01930964、EP01972613、EP01997799、EP02011790、EP02055700、
EP02055701、EP1725079、EP2085382、EP2660300、EP650955、JP07-073529、JP2005112765、
JP2007091719、JP2008021687、JP2014-009196、KR20110088898、KR20130077473、
TW201139402、US06517957、US20020158242、US20030162053、US20050123751、
US20060182993、US20060240279、US20070145888、US20070181874、US20070278938、
US20080014464、US20080091025、US20080106190、US20080124572、US20080145707、
US20080220265、US20080233434、US20080303417、US2008107919、US20090115320、
US20090167161、US2009066235、US2011007385、US20110163302、US2011240968、
US2011278551、US2012205642、US2013241401、US20140117329、US2014183517、US5061569、
US5639914、WO05075451、WO07125714、WO08023550、WO08023759、WO2009145016、
WO2010061824、WO2011075644、WO2012177006、WO2013018530、WO2013039073、
WO2013087142、WO2013118812、WO2013120577、WO2013157367、WO2013175747、
WO2014002873、WO2014015935、WO2014015937、WO2014030872、WO2014030921、
WO2014034791、WO2014104514、WO2014157018。
EBL：
Electronic barrier layer (EBL) can be reducing the number of the electronics and/or exciton that leave emission layer.Stop with lacking
The similar device of layer is compared, and the presence of such barrier layer in a device can produce generally higher efficiency and/or longer
Life-span.In addition it is possible to use barrier layer will launch the desired zone for being limited to OLED.In certain embodiments, with it is closest
The emitter at EBL interfaces is compared, and EBL material has higher LUMO (being closer to vacuum level) and/or compared with high triplet energy.
In some embodiments, compared with the one or more in the main body closest to EBL interfaces, there is EBL material higher LUMO (relatively to connect
Nearly vacuum level) and/or compared with high triplet energy.In an aspect, compound used in EBL contain with it is described below
An identical molecule used or identical functional group in main body.
Main body：
The luminescent layer of the organic el device of the present invention preferably at least contains metal complex as luminescent material, and can
To contain the material of main part for using metal complex as dopant material.The example of material of main part is not particularly limited, and
Any metal complex or organic compound can be used, as long as the triplet energies of main body are more than the triplet energies of dopant
.Any material of main part can be used together with any dopant, as long as meeting triplet criterion.
The example of metal complex as main body preferably has below general formula：
Wherein Met is metal；(Y103-Y104) it is bidentate ligand, Y103And Y104Independently selected from C, N, O, P and S；L101It is
Another part；K' is 1 integer value for arriving the maximum part number that can be connected with metal；And k'+k " is can be connected with metal
Maximum part number.
In an aspect, metal complex is：
Wherein (O-N) is with the bidentate ligand with the metal of O and N Atomic coordinates.
In another aspect, Met is selected from Ir and Pt.In another aspect, (Y103-Y104) it is carbene ligands.
The example of other organic compounds as main body is selected from：The group being made up of aromatic hydrocarbon cyclic compound, such as
Benzene, biphenyl, terphenyl, triphenylene, four sub- benzene, naphthalene, En, Fu, phenanthrene, fluorenes, pyrene,And Azulene；By aromatic heterocyclic compounds group
Into group, such as dibenzothiophenes, dibenzofurans, dibenzo selenophen, furans, thiophene, benzofuran, benzothiophene, benzo
Selenophen, carbazole, indolocarbazole, pyridine radicals indoles, the pyridine of pyrrolo- two, pyrazoles, imidazoles, triazole, oxazole, thiazole, oxadiazoles,
Dislike triazole, dioxazole, thiadiazoles, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazines, evil thiazine, oxadiazines, indoles, benzo miaow
Azoles, indazole, indolizine, benzoxazoles, benzo isoxazole, benzothiazole, quinoline, isoquinolin, cinnolines, quinazoline, quinoxaline, naphthalene
Pyridine, phthalazines, pyridine of talking endlessly, xanthene, acridine, azophenlyene, phenthazine, phenoxazine, benzofuran and pyridine, furans and two pyridines, benzo
Thienopyridine, the pyridine of thieno two, benzo selenophen and pyridine and selenophen and two pyridines；And by 2 to 10 cyclic structure lists
The group of member composition, the cyclic structural unit are same type or difference selected from aromatic cyclic hydrocarbon group and aromatic heterocycle
The group of type and directly or via oxygen atom, nitrogen-atoms, sulphur atom, silicon atom, phosphorus atoms, boron atom, chain structure unit
It is bonded each other with least one in aliphatic ring group.Each selection in each group can with it is unsubstituted or can by selected from
The substituent substitution of the group consisted of：Deuterium, halogen, alkyl, cycloalkyl, miscellaneous alkyl, aralkyl, alkoxy, aryloxy group,
Amino, silylation, alkenyl, cycloalkenyl group, miscellaneous thiazolinyl, alkynyl, aryl, heteroaryl, acyl group, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulphur
Base, sulfinyl, sulfonyl, phosphino- and its combination.
In an aspect, host compound contains at least one in following group in the molecule：
Wherein R101To R107In each independently selected from the group consisted of：Hydrogen, deuterium, halogen, alkyl, cycloalkanes
Base, miscellaneous alkyl, aralkyl, alkoxy, aryloxy group, amino, silylation, alkenyl, cycloalkenyl group, miscellaneous thiazolinyl, alkynyl, aryl, heteroaryl
Base, acyl group, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfenyl, sulfinyl, sulfonyl, phosphino- and its combination, and when it is aryl
Or during heteroaryl, it has the definition similar with above-mentioned Ar.K is 0 to 20 or 1 to 20 integer；K " ' is 0 to 20 integer.
X101To X108Selected from C (including CH) or N.
Z101And Z102Selected from NR101, O or S.
Can with combination of materials disclosed herein be used for OLED in material of main part non-limiting examples with openly
The bibliography of those materials illustrates as follows together：EP2034538、EP2034538A、EP2757608、JP2007254297、
KR20100079458、KR20120088644、KR20120129733、KR20130115564、TW201329200、
US20030175553、US20050238919、US20060280965、US20090017330、US20090030202、
US20090167162、US20090302743、US20090309488、US20100012931、US20100084966、
US20100187984、US2010187984、US2012075273、US2012126221、US2013009543、
US2013105787、US2013175519、US2014001446、US20140183503、US20140225088、
US2014034914、US7154114、WO2001039234、WO2004093207、WO2005014551、WO2005089025、
WO2006072002、WO2006114966、WO2007063754、WO2008056746、WO2009003898、
WO2009021126、WO2009063833、WO2009066778、WO2009066779、WO2009086028、
WO2010056066、WO2010107244、WO2011081423、WO2011081431、WO2011086863、
WO2012128298、WO2012133644、WO2012133649、WO2013024872、WO2013035275、
WO2013081315, WO2013191404, WO2014142472,
Other emitters：
One or more other emitter dopants can be used in combination with the compounds of this invention.Other emitter dopants
Example be not particularly limited, and any compound can be used, as long as compound is typically used as emitter material.Close
The example of suitable emitter material (i.e. TADF, can be including but not limited to also referred to as via phosphorescence, fluorescence, hot activation delayed fluorescence
For E types delayed fluorescence), triplet-triplet is eliminated or the combination of these techniques produces the compound of transmitting.
The non-limiting examples for the emitter material that can be used for combination of materials disclosed herein in OLED and public affairs
Open those materials bibliography illustrate together it is as follows：CN103694277、CN1696137、EB01238981、EP01239526、
EP01961743、EP1239526、EP1244155、EP1642951、EP1647554、EP1841834、EP1841834B、
EP2062907、EP2730583、JP2012074444、JP2013110263、JP4478555、KR1020090133652、
KR20120032054、KR20130043460、TW201332980、US06699599、US06916554、US20010019782、
US20020034656、US20030068526、US20030072964、US20030138657、US20050123788、
US20050244673、US2005123791、US2005260449、US20060008670、US20060065890、
US20060127696、US20060134459、US20060134462、US20060202194、US20060251923、
US20070034863、US20070087321、US20070103060、US20070111026、US20070190359、
US20070231600、US2007034863、US2007104979、US2007104980、US2007138437、
US2007224450、US2007278936、US20080020237、US20080233410、US20080261076、
US20080297033、US200805851、US2008161567、US2008210930、US20090039776、
US20090108737、US20090115322、US20090179555、US2009085476、US2009104472、
US20100090591、US20100148663、US20100244004、US20100295032、US2010102716、
US2010105902、US2010244004、US2010270916、US20110057559、US20110108822、
US20110204333、US2011215710、US2011227049、US2011285275、US2012292601、
US20130146848、US2013033172、US2013165653、US2013181190、US2013334521、
US20140246656、US2014103305、US6303238、US6413656、US6653654、US6670645、US6687266、
US6835469、US6921915、US7279704、US7332232、US7378162、US7534505、US7675228、
US7728137、US7740957、US7759489、US7951947、US8067099、US8592586、US8871361、
WO06081973、WO06121811、WO07018067、WO07108362、WO07115970、WO07115981、WO08035571、
WO2002015645、WO2003040257、WO2005019373、WO2006056418、WO2008054584、
WO2008078800、WO2008096609、WO2008101842、WO2009000673、WO2009050281、
WO2009100991、WO2010028151、WO2010054731、WO2010086089、WO2010118029、
WO2011044988、WO2011051404、WO2011107491、WO2012020327、WO2012163471、
WO2013094620、WO2013107487、WO2013174471、WO2014007565、WO2014008982、
WO2014023377、WO2014024131、WO2014031977、WO2014038456、WO2014112450。
HBL：
Hole blocking layer (HBL) can leave hole and/or the number of exciton of emission layer to reduce.Stop with lacking
The similar device of layer is compared, and the presence of such barrier layer in a device can produce generally higher efficiency and/or longer
Life-span.In addition it is possible to use barrier layer will launch the desired zone for being limited to OLED.In certain embodiments, with it is closest
The emitter at HBL interfaces is compared, and HBL materials have relatively low HOMO () away from vacuum level farther out and/or compared with high triplet energy.
In some embodiments, compared with the one or more in the main body closest to HBL interfaces, HBL materials have relatively low HOMO (away from true
Unoccupied level is farther out) and/or compared with high triplet energy.
In an aspect, compound used in HBL contain with main body described above used in identical molecule or phase
Same functional group.
In another aspect, compound used in HBL contains at least one in following group in the molecule：
Wherein k is 1 to 20 integer；L101It is another part, k' is 1 to 3 integer.
ETL：
Electron transfer layer (ETL) can include the material that can transmit electronics.Electron transfer layer can be it is intrinsic (without
Doping) or it is doped.Electric conductivity can be strengthened using doping.The example of ETL materials is not particularly limited, and can be with
Using any metal complex or organic compound, as long as it is generally transmitting electronics.
In an aspect, compound used in ETL contains at least one in following group in the molecule：
Wherein R101Selected from the group consisted of：Hydrogen, deuterium, halogen, alkyl, cycloalkyl, miscellaneous alkyl, aralkyl, alcoxyl
Base, aryloxy group, amino, silylation, alkenyl, cycloalkenyl group, miscellaneous thiazolinyl, alkynyl, aryl, heteroaryl, acyl group, carbonyl, carboxylic acid, ester,
Nitrile, isonitrile, sulfenyl, sulfinyl, sulfonyl, phosphino- and its combination, when it is aryl or heteroaryl, it has and above-mentioned Ar
Similar definition.Ar1To Ar3With the definition similar with Ar referred to above.K is 1 to 20 integer.X101To X108Selected from C
(including CH) or N.
In another aspect, metal complex used in ETL contains (but not limited to) below general formula：
Wherein (O-N) or (N-N) are that have and atom O, N or N, the bidentate ligand of the metal of N coordinations；L101It is another
Part；K' is 1 integer value for arriving the maximum part number that can be connected with metal.
The non-limiting examples for the ETL materials that can be used for combination of materials disclosed herein in OLED are with disclosing that
The bibliography of a little materials illustrates as follows together：CN103508940、EP01602648、EP01734038、EP01956007、
JP2004-022334、JP2005149918、JP2005-268199、KR0117693、KR20130108183、
US20040036077、US20070104977、US2007018155、US20090101870、US20090115316、
US20090140637、US20090179554、US2009218940、US2010108990、US2011156017、
US2011210320、US2012193612、US2012214993、US2014014925、US2014014927、
US20140284580、US6656612、US8415031、WO2003060956、WO2007111263、WO2009148269、
WO2010067894、WO2010072300、WO2011074770、WO2011105373、WO2013079217、
WO2013145667, WO2013180376, WO2014104499, WO2014104535,
Charge generation layer (CGL)
In connecting or stacking OLED, CGL plays basic role to performance, and it injects electronics and the warp in hole by being respectively used to
The layer of n doping and the layer composition through p doping.Electronics and hole are supplied by CGL and electrode.The electronics that is consumed in CGL and hole by
Refilled respectively from negative electrode and anode injected electrons and hole；Then, bipolar current progressivelyes reach stable state.Typical CGL
Material includes n and p conductivity dopants used in transport layer.
In each layer of OLED device in any compound referred to above used, hydrogen atom can be partly or completely
Perdeuterated.Therefore, any substituent specifically listed, such as (but not limited to) methyl, phenyl, pyridine radicals etc. can be its non-deuteriums
Change, part deuterate and and complete deuterated form.Similarly, substituent classification (such as (but not limited to) alkyl, aryl, cycloalkanes
Base, heteroaryl etc.) it can also be its non-deuterate, part deuterate and complete deuterated form.
Experiment
1. materials synthesis
2. chemical abbreviations used are as follows in whole this document：
3.Pd2(dba)3For three (dibenzalacetone) two palladium (0),
4.SPhos is dicyclohexyl (2', 6'- dimethoxy-[1,1'- biphenyl] -2- bases) phosphine, and
Ir(LB91)2The synthesis of (part 2)
The synthesis of the bromo- 9,9,10,10- tetramethyls -9,10- dihydroanthracenes of 2-
Titanium chloride (IV) (62.7ml, 62.7mmol) is added into the three neck round bottom of drying.In N2Under take off solution
Gas and it is cooled to -40 DEG C.Zinc methide (50.2ml, 100mmol) is added dropwise.Mixture is stirred at the same temperature
20min.It will then be added dropwise in 250mL DCM.2- bromine anthracene -9,10- diketone (3.6g, 12.54mmol).Allow reaction mixed
Compound is warming up to room temperature and stirred overnight.Reaction flask is cooled to 0 DEG C and is quenched with MeOH.Mixture is diluted with water simultaneously
And extracted with DCM.With the organic phase of salt water washing ECDC simultaneously.After removing solvent, crude product is adsorbed on diatomite and
Purified by flash chromatography (heptane), obtain tetramethyl -9, the 10- dihydroanthracene of 2- bromines 9,9,10,10- (2g, 50%).
2- phenyl -4- (ring-the 2- of 4,4,5,5- tetramethyl -1,3,2- dioxas boron penta are added into 100ml round-bottomed flasks
Base) pyridine (3.92g, 13.96mmol), tetramethyl -9, the 10- dihydroanthracenes (2.2g, 6.98mmol) of 2- bromo- 9,9,10,10-,
SPhos (0.229g, 0.558mmol), Pd2dba3(0.128g, 0.140mmol), DME (50ml) and water (5.00ml).Use N2Make
Reactant mixture deaerates 15 minutes.In N2Lower backflow heating response mixture is overnight.After reaction flask is cooled into room temperature, use
EtOAc extractive reaction mixtures, and the organic phase with salt water washing ECDC simultaneously.After removing solvent, crude product is adsorbed in
On diatomite and by flash chromatography (heptane/THF, 9:1) purify, acquisition 2- phenyl -4- (9,9,10,10- tetramethyl -9,
10- dihydroanthracene -2- bases) pyridine (1.3g, 98%).
By iridium tripolymer (2.5g, 3.20mmol) and 2- phenyl -4- (9,9,10,10- tetramethyl -9,10- dihydroanthracene -2-
Base) pyridine (2.491g, 6.39mmol) is added in MeOH (45ml) and EtOH (45.0ml) mixture.Use N2Make mixture
Deaerate 20 minutes and in N2Under be heated to the lasting 70h of (80 DEG C) of backflow.Short filter solid was filled in by diatomaceous.Yellow is consolidated
Body is dissolved in DCM.Remove solvent after, by residue be coated on diatomite and by flash chromatography (toluene/heptane,
7:3) purify, produce Ir (LB91)2(part 2).
Device example
All devices all pass through high vacuum (about 10-7Support) thermal evaporation manufacture.Anode electrode is 80nm tin indium oxide
(ITO).Cathode electrode is made up of 1nm LiF followed by 100nm Al.After the fabrication, immediately nitrogen glove box (<1ppm
H2O and O2) in all devices are encapsulated with the glass cover that is sealed through epoxy resin, and moisture absorption gas agent is incorporated into packaging
Portion.
One group of device example has the organic stacking sequentially consisted of from ITO surfaces：10nm LG101 (comes from LG
Chemical (LG Chem)) hole injection layer (HIL) is used as, 50nm PPh-TPD is as hole transmission layer (HTL), 40nm transmitting
Layer (EML), the aDBT-ADN with 35 weight %LiQ followed by 35nm is as electron transfer layer (ETL).EML has three kinds
Component：88 weight % EML is main body (60 weight %H-1 and 40 weight %H-2) mixture；And 12 weight % EML
It is that the compounds of this invention or comparative compound (CC-1 and CC-2) are used as emitter.The chemical constitution displaying of compound used therefor is such as
Under.
The general introduction for the device data that device example records under 9000 nits is provided in table 1 below.
Table 1
| Device ID | Dopant | Color | Voltage [V] | LE[cd/A] | PE[lm/W] | EQE (%) |
| Device 1 | Ir(LB91)2Part 2 | Yellow | 1.00 | 1.19 | 1.19 | 1.19 |
| Device C-1 | CC-1 | Yellow | 1.00 | 1.00 | 1.00 | 1.00 |
| Device C-2 | CC-2 | Yellow | 1.04 | 0.95 | 0.90 | 0.93 |
Data in table 1 are shown, compared with comparative example (CC-1 and CC-2), emitter is used as using the compounds of this invention
Device same hue but more efficient is realized under identical voltage.Between present example and comparative example (CC-1) only
One difference is the substitution of 9,9,10,10- tetramethyl -9,10- dihydroanthracenes, and it is possible be attributed to emitter in device poly-
Collection is reduced and alignment strengthens and realizes the key of higher device efficiency.
It should be understood that various embodiments described herein is only by means of example, and it is not limiting as the scope of the present invention.
For example, many materials as described herein can be substituted with other materials and structure in the case of without departing substantially from the spirit of the present invention
Material and structure.As requested therefore the present invention can include the change shape of instantiation as described herein and preferred embodiment
Formula, such as it will be apparent to those skilled in the art that.It should be understood that the various theoretical and unawareness why worked on the present invention
Figure is restricted.
Claims (15)
1. a kind of composition, it includes the first compound；
Wherein described first compound can serve as the emitter in organic light emitting apparatus at room temperature；
Wherein described first compound includes at least one aromatic ring and at least one substituent R；
Each in wherein described at least one R is directly bonded to one in the aromatic ring；
Each in wherein described at least one R has following formula：
Wherein L is direct key or organo linking group；
Wherein X1And X2It is each independently selected from the group being made up of carbon and silicon；
Wherein R1And R2Each represent monosubstituted to possible the maximum number of substituted or unsubstituted；
Wherein R1To R6It is each independently selected from the group consisted of：Hydrogen, deuterium, halogen, alkyl, cycloalkyl, miscellaneous alkyl, virtue
Alkyl, alkoxy, aryloxy group, amino, silylation, alkenyl, cycloalkenyl group, miscellaneous thiazolinyl, alkynyl, aryl, heteroaryl, acyl group, carbonyl,
Carboxylic acid, ester, nitrile, isonitrile, sulfenyl, sulfinyl, sulfonyl, phosphino- and its combination；And
Wherein R3To R6Any neighbouring substituent optionally engage or condense cyclization.
2. composition according to claim 1, wherein L are direct key or the organic linking selected from the group consisted of
Group：Aryl, substituted aryl, heteroaryl, substituted heteroaryl and its combination.
3. composition according to claim 1, wherein X1And X2For carbon；Or X1For carbon and X2For silicon.
4. composition according to claim 1, wherein R3To R6It is each independently selected from the group consisted of：Alkyl,
Cycloalkyl, its partly or completely variant of perdeuterated, its partly or completely variant of perfluorinate and its combination.
5. composition according to claim 1, wherein first compound is the metal-complexing network for having metal-carbon key
Compound, wherein the metal is selected from the group consisted of：Ir, Rh, Re, Ru, Os, Pt, Au and Cu.
6. composition according to claim 1, wherein first compound has formula M (L1)x(L2)y(L3)z；
Wherein L1、L2And L3Can be with identical or different；
Wherein L1、L2And L3In it is at least one be not acetyl pyruvate part；
Wherein x is 1,2 or 3；
Wherein y is 0,1 or 2；
Wherein z is 0,1 or 2；
Wherein x+y+z is the oxidation state of the metal M；
Wherein L1、L2And L3It is each independently selected from the group consisted of：
Wherein each X1To X17Independently selected from the group being made up of carbon and nitrogen；
Wherein X is selected from the group consisted of：BR', NR', PR', O, S, Se, C=O, S=O, SO2, CR'R ", SiR'R " and
GeR'R”；
Wherein R' and R " is optionally condensed or engaged to form ring；
Wherein each Ra、Rb、RcAnd RdIt can represent monosubstituted to possible the maximum number of substituted or unsubstituted；
Wherein R', R ", Ra、Rb、RcAnd RdIt is each independently selected from the group consisted of：Hydrogen, deuterium, halogen, alkyl, cycloalkanes
Base, miscellaneous alkyl, aralkyl, alkoxy, aryloxy group, amino, silylation, alkenyl, cycloalkenyl group, miscellaneous thiazolinyl, alkynyl, aryl, heteroaryl
Base, acyl group, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfenyl, sulfinyl, sulfonyl, phosphino- and its combination；And
Wherein Ra、Rb、RcAnd RdAny two optionally condense or engage adjacent to substituent with formed ring or formed multidentate ligand；And
And
Wherein described Ra、Rb、RcAnd RdIn it is at least one including at least one R.
7. composition according to claim 6, wherein first compound has Formulas I r (L1)2(L2), wherein L1And L2
It is different and be each independently selected from the group consisted of：
8. composition according to claim 1, wherein each at least one R is independently selected from by with the following group
Into group：
9. composition according to claim 6, wherein L1、L2And L3In it is at least one selected from the group consisted of：
10. composition according to claim 6, wherein L1、L2And L3In it is at least one selected from the group consisted of
Group：
11. composition according to claim 10, wherein the compound is with Formulas I r (part i) (LBj)2Chemical combination
Thing x；
Wherein x=300i+j-300；I is 1 to 135 integer, and j is 1 to 300 integer；And wherein LB1To LB300Tool
There is following structure：
12. a kind of organic light emitting apparatus OLED, it is included：
Anode；
Negative electrode；With
Organic layer, it is placed between the anode and the negative electrode, includes the first compound；
Wherein described first compound can serve as the emitter in organic light emitting apparatus at room temperature；
Wherein described first compound includes at least one aromatic ring and at least one substituent R；
Each in wherein described at least one R is directly bonded to one in the aromatic ring；
Each in wherein described at least one R has following formula：
Wherein L is direct key or organo linking group；
Wherein X1And X2It is each independently selected from the group being made up of carbon and silicon；
Wherein R1And R2Each represent monosubstituted to possible the maximum number of substituted or unsubstituted；
Wherein R1To R6It is each independently selected from the group consisted of：Hydrogen, deuterium, halogen, alkyl, cycloalkyl, miscellaneous alkyl, virtue
Alkyl, alkoxy, aryloxy group, amino, silylation, alkenyl, cycloalkenyl group, miscellaneous thiazolinyl, alkynyl, aryl, heteroaryl, acyl group, carbonyl,
Carboxylic acid, ester, nitrile, isonitrile, sulfenyl, sulfinyl, sulfonyl, phosphino- and its combination；And
Wherein R3To R6Any neighbouring substituent optionally engage or condense cyclization.
13. OLED according to claim 12, wherein the organic layer further comprises main body, wherein main body includes at least
One chemical group selected from the group consisted of：Triphenylene, carbazole, dibenzothiophenes, dibenzofurans, dibenzo selenium
Fen, azepine-triphenylene, azepine carbazole, azepine-dibenzothiophenes, azepine-dibenzofurans and azepine-dibenzo selenophen, or institute
State main body and be selected from the group consisted of：
With its combination.
14. a kind of consumer product, it includes organic light emitting apparatus, wherein the organic light emitting apparatus includes：
Anode；
Negative electrode；With
Organic layer, it is placed between the anode and the negative electrode, includes the first compound；
Wherein described first compound can serve as the emitter in organic light emitting apparatus at room temperature；
Wherein described first compound includes at least one aromatic ring and at least one substituent R；
Each in wherein described at least one R is directly bonded to one in the aromatic ring；
Each in wherein described at least one R has following formula：
Wherein L is direct key or organo linking group；
Wherein X1And X2It is each independently selected from the group being made up of carbon and silicon；
Wherein R1And R2Each represent monosubstituted to possible the maximum number of substituted or unsubstituted；
Wherein R1To R6It is each independently selected from the group consisted of：Hydrogen, deuterium, halogen, alkyl, cycloalkyl, miscellaneous alkyl, virtue
Alkyl, alkoxy, aryloxy group, amino, silylation, alkenyl, cycloalkenyl group, miscellaneous thiazolinyl, alkynyl, aryl, heteroaryl, acyl group, carbonyl,
Carboxylic acid, ester, nitrile, isonitrile, sulfenyl, sulfinyl, sulfonyl, phosphino- and its combination；And
Wherein R3To R6Any neighbouring substituent optionally engage or condense cyclization.
15. consumer product according to claim 14, wherein the consumer product is selected from the group consisted of：
Flat-panel monitor, computer monitor, medical monitors, television set, billboard, for it is internal or external illumination and/or transmit
Number lamp, head-up display, all-transparent or partially transparent display, flexible display, laser printer, phone, mobile electricity
Words, tablet PC, flat board mobile phone, personal digital assistant PDA, wearable device, laptop computer, digital camera, shooting
Machine, view finder, miniscope, 3-D displays, virtual reality or augmented reality display, the vehicles, include multiple tilings
Video wall, theater or the stadium screen of display together, and direction board.
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| CN111925397A (en) * | 2019-05-13 | 2020-11-13 | 环球展览公司 | Organic electroluminescent material and device |
| CN111987233A (en) * | 2019-05-24 | 2020-11-24 | 环球展览公司 | Organic electroluminescent material and device |
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Also Published As
| Publication number | Publication date |
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| CN107868109B (en) | 2021-07-27 |
| US10680187B2 (en) | 2020-06-09 |
| CN113563385A (en) | 2021-10-29 |
| KR20180033094A (en) | 2018-04-02 |
| US20180130962A1 (en) | 2018-05-10 |
| EP3323822B1 (en) | 2019-08-28 |
| EP3323822A1 (en) | 2018-05-23 |
| KR102490187B1 (en) | 2023-01-18 |
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